Heterocyclic 2-alkoxyphenoxysulfonylureas and the use thereof as herbicides or plant growth regulators

ABSTRACT

Compounds of the formula I or salts thereof ##STR1## where R 1  is ethyl, propyl or isopropyl, 
     R 2  is halogen, NO 2 , CF 3 , CN, alkyl, alkoxy, alkylthio or alkoxycarbonyl, 
     n is 0, 1, 2 or 3, Y is O or S, 
     R 3  is hydrogen, alkyl, alkenyl, alkynyl or alkoxy; 
     R 4  is a heterocyclic radical of the formulae ##STR2## E is CH or N; G is O or CH 2 , R 5  and R 6  are hydrogen, halogen, or are alkyl, alkoxy or alkylthio, which are optionally substituted by halogen, alkoxy or alkylthio, or are --NR 12  R 13 , --OCHR 7  --CO 2  R 12 , (C 3  -C 6  cycloalkyl, (C 3  -C 5 )alkenyl, (C 2  -C 4 ) -alkynyl, (C 3  -C 5 )alkenyloxy or (C 3  -C 5  (alkynyloxy; R 7  is hydrogen or alkyl, R 8  is alkyl, --CHF 2  or --CH 2  CF 3  ; R 9  and R 10  are hydrogen, alkyl, alkoxy or halogen; R 11  is hydrogen, alkyl, --CHF 2  or CH 2  CF 3  ; R 12  and R 13  independently of one another are hydrogen, alkyl, alkenyl or alkynyl, possess outstanding herbicidal and plant growth-regulating properties.

DESCRIPTION

It is known that heterocyclically substituted phenoxysulfonylureas possess herbicidal and plant growth-regulating properties (EP-A 4,163, DE-A 3,151-450).

Surprisingly, it has now been found that heterocyclically substituted sulfamic acid phenyl esters, the phenyl ester moiety of which is formed by selected pyrocatechol monoalkyl ethers, are particularly suitable as herbicides or plant growth regulators.

The present invention therefore relates to compounds of the formula (I) or the salts thereof ##STR3## where

R¹ is ethyl, propyl or isopropyl,

R² is halogen, NO₂, CF₃, CN, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, (C₁ -C₄)alkylthio or (C₁ -C₄ -alkoxy)carbonyl,

n is 0, 1, 2 or 3,

Y is O or S,

R³ is hydrogen, (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl, (C₂ -C₈)alkynyl or (C₁ -C₄)alkoxy;

R⁴ is a heterocyclic radical of the formulae ##STR4##

E is CH or N,

G is O or CH₂,

R⁵ and R⁶ independently of one another are hydrogen, halogen, (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy or (C₁ -C₆)alkylthio, it being possible for the abovementioned radicals to be monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio, furthermore are a radical of the formula --NR¹² R¹³, --OCHR⁷ --CO₂ R¹², (C₃ -C₆)cycloalkyl, (C₃ -C₅)alkenyl, (C₂ -C₄ )alkynyl, (C₃ -C₅)alkenyloxy or (C₃ -C₅)alkynyloxy,

R⁷ is hydrogen or (C₁ -C₄)alkyl,

R⁸ is (C₁ -C₄)alkyl, --CHF₂ or --CH₂ CF₃,

R⁹ and R¹⁰ independently of one another are hydrogen, (C₁ -C₄)alkyl, (C₁ -C₅)alkoxy or halogen,

R¹¹ is hydrogen, (C₁ -C₄)alkyl, --CHF₂ or CH₂ CF₃ and

R¹² and R¹³ independently of one another are hydrogen, (C₁ -C₄)alkyl, (C₂ -C₄)alkenyl or (C₃ -C₄)alkynyl.

The compounds of the formula (1) can form salts in which the hydrogen of the --SO₂ --NH-- group is replaced by a cation which is suitable for agriculture. In general, these salts are metal salts, in particular alkali metal salts, alkaline earth metal salts, optionally alkylated ammonium salts or organic amine salts.

In the above definitions, halogen is preferably fluorine, chlorine or bromine.

Preferred compounds of the formula I or salts thereof are those in which n=0 or 1, Y is O, R² is orientated in the 6-position of the phenyl ring and has the above-mentioned meaning, in the case of halogen in particular F or Cl, R³ is hydrogen, (C₁ -C₄)alkyl or (C₃ -C₄)alkenyl, R⁴ is a heterocyclic radical of the formula ##STR5## E is CH or N and R⁵ and R⁶ are halogen, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio, each of which can be substituted as described above.

Particularly preferred compounds of the formula (I) or salts thereof are those where n=0 or 1, R² is orientated in the 6-position of the phenyl ring and is fluorine, chlorine, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy or (C₁ -C₄)alkoxycarbonyl, R³ is hydrogen or methyl, R⁴ is a heterocyclic radical of the formula ##STR6## E is CH or N and R⁵ and R⁶ independently of one another are chlorine, bromine, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, OCHF₂ or OCH₂ CF₃ or CF₃, in particular (C₁ -C₂)alkyl or (C₁ -C₂)alkoxy.

The present invention furthermore relates to processes for the preparation of the compounds of the general formula (I) or salts thereof, which comprise reacting

(a) a compound of the formula (II) ##STR7## with a compound of the formula (III) ##STR8## or

(b) a compound of the formula (IV) ##STR9## with a chlorosulfonylurea of the formula (V) ##STR10## or

(c) a compound of the formula (VI) ##STR11## with a carbamate of the formula (VII) ##STR12## where Z is phenyl or (C₁ -C₆)alkyl and, if desired, converting the resulting compounds of the formula I into their salts.

The reaction of the compounds of the formulae (II) and (III) is preferably carried out in inert aprotic solvents, such as, for example, acetonitrile, dichloromethane, toluene, tetrahydrofuran or dioxane, at temperatures between 0° C. and the boiling point of the solvent.

The phenoxysulfonyl isocyanates of the formulae (II) can be prepared in a simple manner by processes which are known in principle from the corresponding pyrocatechol monoethers of the formula (IV) and chlorosulfonyl isocyanate (cf. G. Lohaus, Chem. Ber. 105. 2791 (1972)).

The starting substances of the formula (III) are known or can be prepared by processes which are known in principle, for example by cyclizing corresponding guanidine derivatives with appropriately substituted 1,3-diketones, cf., for example, "The Chemistry of Heterocyclic Compounds", Vol. XVI (1962) and Supplement I (1970), or by derivatization of cyanuric chloride, cf., for example, "The Chemistry of Heterocyclic Compounds", L. Rapaport: "s-Triazines and Derivatives" (1959).

The reaction of the compounds (IV) with the chlorosulfonylureas (V) is preferably carried out in inert solvents, such as, for example, dichloromethane, at temperatures between -10° C. and 80° C. in the presence of a base as the HCl-binding agent. Bases which can be employed are alkali metal carbonates, alkali metal bicarbonates, alkaline earth metal carbonates or alkaline earth metal bicarbonates, such as, for example, K₂ CO₃, NaHCO₃ or Na₂ CO₃, or tertiary amines, such as, for example, pyridine or triethylamine.

The pyrocatechol monoethers (IV) are known from the literature or can be prepared by processes which are known from the literature. The chlorosulfonylureas (V) are accessible from the amines of the formula (III) and chlorosulfonyl isocyanate (EP-A 141,199).

The reaction of the compounds (VI) with the heterocyclic carbamates of the formula (VII) is preferably carried out in the presence of tertiary organic bases, such as, for example, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), in inert solvents, such as acetonitrile or dioxane, at temperatures between 20° C. and the boiling point of the solvent (analogously to EP-A 44,807).

The carbamates (VII) which are required for this are known from the literature or are prepared by known processes (EP-A 70,804). The sulfamates (VI) are prepared from the pyrocatechol monoethers on which they are based by known processes (cf., for example, Synthesis 1978, 357; Z. Chem. 15, 270 (1975); Chem. Ber. 105, 2791 (1972)).

The salts of the compounds of the formula I are preferably prepared in inert solvents, such as, for example, water, methanol or acetone, at temperatures from 0°-100° C. Examples of bases which are suitable for the preparation of the salts according to the invention are alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, ammonia or ethanolamine.

The compounds of the formula I according to the invention have an excellent herbicidal activity against a broad range of economically important monocotyledon and dicotyledon noxious plants. The active substances act equally well on perennial weeds which produce shoots from rhizomes, rootstocks or other perennial organs and which cannot be easily controlled. In this context, it does not matter if the substances are applied before sowing, as a pre-emergence treatment or post-emergence treatment. Some representatives of the monocotyledon and dicotyledon weed flora which can be controlled may be mentioned individually as examples, but this is not to be taken to mean a restriction to certain species.

The monocotyledon weed species controlled include, for example, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria etc. and Cyperus species from the annual group, and the perennial species include Agropyron, Cynodon, Imperata and Sorghum etc., and also perennial Cyperus species. Of the dicotyledon weed species, the range of action covers Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon, Sida etc. from the annual plants, and Convolvulus, Cirsium, Rumex, Artemisia etc. from the perennial weeds.

Excellent control of weeds occurring under the specific culture conditions in rice, such as, for example, Sagittaria, Alisma, Eleocharis, Scirpus, Cyperus etc., by the active substances according to the invention is also possible.

If the compounds according to the invention are applied to the soil surface before germination, either emergence of the weed seedlings is prevented completely, or the weeds grow until they have reached the cotyledon stage but growth then comes to a standstill and, after a period of three to four weeks, the plants eventually die completely.

When, in the post-emergence method, the active substances are applied to the green parts of the plants, growth also stops dramatically very soon after the treatment, and the weed plants remain in the growth stage of the time of application, or, after a certain period of time, die more or less rapidly so that competition by the weeds, which is detrimental for the crop plants, can thus be prevented at a very early stage and in a sustained manner by using the novel agents according to the invention.

Even though the compounds according to the invention have an excellent herbicidal activity against monocotyledon and dicotyledon weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, rice, maize, sugar beet, cotton and soya beans, are damaged to a negligible extent only, or not at all. Thus, the present compounds are very suitable for selectively controlling undesired plant growth in agricultural plantations of useful plants.

In addition, the compounds according to the invention have plant growth-regulating properties in crop plants. They have a regulating effect on the plant metabolism and can thus employed for facilitating harvesting, such as, for example, by provoking desiccation, abscission and stunted growth. Furthermore, they are suitable for generally regulating and inhibiting undesired vegetative growth, without simultaneously destroying the plants. Inhibition of vegetative growth plays an important role in many monocotyledon and dicotyledon crops because lodging can be reduced hereby, or prevented completely.

The agents according to the invention can be employed in the conventional preparations as wettable powders, emulsifiable concentrates, emulsions, sprayable solutions, dusting agents, seed-dressing agents, dispersions, granules or microgranules.

Wettable powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, also contain wetting agents, for example, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkylsulfonates or alkylphenylsulfonates, and dispersing agents, for example, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate and also sodium oleoylmethyltaurinate, as well as, if appropriate, a diluent or inert substance. The formulations are prepared in a customary manner, for example by grinding and mixing of the components.

Emulsifiable concentrates can be prepared, for example, by dissolving the active substance in an inert organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene and also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. In the case of liquid active substances, all or part of the solvent component can be omitted. Emulsifiers which can be used are, for example: calcium salts of alkylarylsulfonic acid, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, fatty alcohol/propylene oxide/ethylene oxide condensation products alkyl polyglycol ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusting agents are obtained by grinding the active substance with finely divided solid substances, for example talc or natural clays, such as kaolin, bentonite, pyrophillite, or diatomaceous earth.

Granules can be produced either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of excipients such as sand, kaolinites or granulated inert material, by means of binders, for example polyvinyl alcohol, sodium polyacrylate or alternatively mineral oils. Suitable active substances can also be granulated in the manner which is conventional for the preparation of fertilizer granules, if desired in a mixture with fertilizers.

The active substance concentration in wettable powders is, for example, about 10 to 90% by weight; the remainder to 100% by weight comprises conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 5 to 80% by weight. Formulations in the form of dusts usually contain 5 to 20% by weight, sprayable solutions about 2 to 20% by weight. In the case of granules, the active substance content depends partly on whether the active compound is liquid or solid and on which granulation auxiliaries, fillers etc. are used.

In addition, the active substance formulations mentioned contain, if appropriate, the adhesives, wetting agents, dispersing agents, emulsifiers, penetrants, solvents, fillers or carriers which are conventional in each case.

For use, the concentrates, present in commercially available form, are diluted, if appropriate, in a conventional manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and, in some cases, also in the case of microgranules. Preparations in the form of dusts and in the form of granules and also sprayable solutions are usually not further diluted with other inert substances before use.

The application rate required varies with the external conditions, such as temperature, humidity amongst others. It can vary within wide limits between, for example 0.005 and 10.0 kg/ha or more of active substance, preferably, however, it is between 0.01 and 5 kg/ha.

If appropriate, mixtures or mixed formulations with other active substances, such as, for example, insecticides, acaricides, herbicides, fertilizers, growth regulators or fungicides are also possible.

The following examples illustrate the invention in greater detail.

FORMULATION EXAMPLES

A. A dusting agent is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc or inert substance, and comminuting the mixture in a hammer mill.

B. A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active substance, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium ligninsulfonte and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding the mixture in a pinned disk mill.

C. A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of active substance with 6 parts by weight of alkylphenol polyglycol ether (®Triton 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to above 377° C.), and grinding the mixture in a ball mill to a fineness of below 5 microns.

D. An emulsifiable concentrate is obtained from 15 parts by weight of active substance, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.

CHEMICAL EXAMPLES EXAMPLE 1

2-Ethoxyphenoxysulfonyl isocyanate

67.9 g (0.48 mol) of chlorosulfonyl isocyanate are added dropwise at 25° C. to a solution of 55.2 g (0.4 mol) of 2-ethoxyphenol in 500 ml of xylene. When the dropwise addition is complete, the temperature is increased slowly to 140° C. and the mixture is refluxed for 2.5 hours. The mixture is cooled, and the solvent as well as excess chlorosulfonyl isocyanate are removed on a rotary evaporator. The yellow oil which remains (97.2 g=100% of theory) is employed without further purification.

EXAMPLE 2

3-(4,6-Dimethoxypyrimidin-2-yl)-1-(2-ethoxyphenoxysulfonyl)urea

A solution of 97.2 g (0.4 mol) of the product of Example 1 in 100 ml of dichloromethane is added dropwise at 25° C. to 62.0 g (0.4 mol) of 2-amino-4,6-dimethoxypyrimidine in 600 ml of dichloromethane. Stirring at room temperature is continued for 16 hours, the mixture is diluted with 600 ml of dichloromethane, and the organic phase is washed twice with 500 ml portions of 2N hydrochloric acid and once with 500 ml of water. After the mixture has been dried using sodium sulfate and after the solvent has been removed on a rotary evaporator, an oily product remains which crystallizes on trituration with diethyl ether. 145.0 g (91% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-ethoxyphenoxysulfonyl)urea of melting point 145°-147° C. are obtained.

EXAMPLE 3

3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-propoxyphenoxysulfonyl)urea

1.74 g (0.008 mol) of 2-propoxyphenyl sulfamate are added at room temperature to 2.32 g (0.0084 mol) of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate, dissolved in 100 ml of acetonitrile. After 1.33 g (0.0088 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) have been added, the reaction mixture is stirred at room temperature for 18 hours, concentrated, diluted with H₂ O and acidified using 2N hydrochloric acid to give a pH of 3-4. After the solids have been filtered off with suction and dried, 2.85 g (86% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)- 1-(2-propoxyphenoxysulfonyl)urea of melting point 108°-109° C. are obtained.

The compounds of the Tables which follow are prepared as described in Examples 1-3.

                                      TABLE 1                                      __________________________________________________________________________      ##STR13##                                                                     Ex. No.                                                                             R.sup.1                                                                               R.sup.2                                                                               R.sup.3 R.sup.5                                                                              R.sup.6                                                                               E  n m.p. [°C.]                 __________________________________________________________________________      4   CH.sub.2 CH.sub.3                                                                            H       CH.sub.3                                                                             CH.sub.3                                                                              CH 0 162                                5   CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 0 125                                6   CH.sub.2 CH.sub.3                                                                            H       CH.sub.3                                                                             CH.sub.3                                                                              N  0                                    7   CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  0 128-129                            8   CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             N  0 169-170                            9   CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            SCH.sub.3                                                                             N  0                                    10  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            Cl     CH 0 134-135                            11  CH.sub.2 CH.sub.3                                                                            H       OCF.sub.2 H                                                                          CH.sub.3                                                                              CH 0                                    12  CH.sub.2 CH.sub.3                                                                            H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 0 140                                13  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            Br     CH 0                                    14  CH.sub.2 CH.sub.3                                                                            H       CH.sub.3                                                                             Cl     CH 0 163                                15  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            H      CH 0                                    16  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            NHCH.sub.3                                                                            CH 0                                    17  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            NHCH.sub.3                                                                            N  0                                    18  CH.sub.2 CH.sub.3                                                                            H       CH.sub.3                                                                             NHCH.sub.3                                                                            CH 0                                    19  CH.sub.2 CH.sub.3                                                                            H       OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                                                            N  0 168                                20  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            SCH.sub.3                                                                             CH 0                                    21  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                      CH 0                                    22  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            OC.sub.3 H.sub.7                                                                      CH 0                                     23 CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                      N  0                                    24  CH.sub.2 CH.sub.3                                                                            H       Cl    OC.sub.2 H.sub.5                                                                      CH 0                                    25  CH.sub.2 CH.sub.3                                                                            H       OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                      CH 0                                    26  CH.sub.2 CH.sub.3                                                                            H       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                             CH 0                                    27  CH.sub.2 CH.sub.3                                                                            H       CF.sub.3                                                                             OCH.sub.3                                                                             CH 0                                    28  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.2 CF.sub.3                                                                   CH.sub.3                                                                              CH 0                                    29  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             CH 0                                    30  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.2 CF.sub.3                                                                    CH 0                                    31  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.2 CF.sub.3                                                                   NHCH.sub.3                                                                            CH 0                                    32  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             N  0 175                                33  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.2 CF.sub.3                                                                   NHCH.sub.3                                                                            N  0                                    34  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            NHC.sub.2 H.sub.5                                                                     CH 0                                    35  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.2 CF.sub.3                                                                   NHC.sub.2 H.sub.5                                                                     CH 0                                    36  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                     CH 0                                    37  CH.sub.2 CH.sub.3                                                                            H       OCH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                   CH 0                                    38  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       CH.sub.3                                                                             CH.sub.3                                                                              CH 0 113-115                            39  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 0 101-102                            40  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       CH.sub.3                                                                             CH.sub.3                                                                              N  0                                    41  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            CH.sub.3                                                                              N  0  93-123                            42  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            OCH.sub.3                                                                             N  0                                    43  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            Cl     CH 0 121-123                            44  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCF.sub.2 H                                                                          CH.sub.3                                                                              CH 0 126                                45  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 0                                    46  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            Br     CH 0                                    47  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       CH.sub.3                                                                             Cl     CH 0                                    48  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            H      CH 0                                    49  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            NHCH.sub.3                                                                            CH 0                                    50  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            NHCH.sub.3                                                                            N  0                                    51  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       CH3   NHCH.sub.3                                                                            CH 0                                    52  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       CH.sub.3                                                                             NHCH.sub.3                                                                            N  0                                    53  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            SCH.sub.3                                                                             CH 0                                    54  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                      CH 0 127-130                            55  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            OC.sub.3 H.sub.7                                                                      N  0                                    56  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                      N  0                                    57  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       Cl    OC.sub.2 H.sub.5                                                                      CH 0                                    58  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                      CH 0                                    59  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                             CH 0                                    60  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       CF.sub.3                                                                             OCH.sub.3                                                                             CH 0                                    61  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.2 CF.sub.3                                                                   CH.sub.3                                                                              CH 0                                    62  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             CH 0                                    63  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.2 CF.sub.3                                                                    CH 0                                    64  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.2 CF.sub.3                                                                   NHCH.sub.3                                                                            CH 0                                    65  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             N  0                                    66  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.2 CF.sub.3                                                                   NHCH.sub.3                                                                            N  0                                    67  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0                                    68  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.2 CF.sub.3                                                                   NHC.sub.2 H.sub.5                                                                     CH 0                                    69  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                     CH 0                                    70  CH.sub.2 CH.sub.2 CH.sub.3                                                                   H       OCH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                   CH 0                                    71  CH(CH.sub.3).sub.2                                                                           H       CH.sub.3                                                                             CH.sub.3                                                                              CH 0  90-92                             72  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 0 135-137                            73  CH(CH.sub.3).sub.2                                                                           H       CH.sub.3                                                                             CH.sub.3                                                                              N  0                                    74  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  0 108-110                            75  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.2                                                                            OCH.sub.3                                                                             CH 0 141-143                            76  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            Cl     CH 0 121-123                            77  CH(CH.sub.3).sub.2                                                                           H       OCF.sub.2 H                                                                          CH.sub.3                                                                              CH 0                                    78  CH(CH.sub.3).sub.2                                                                           H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 0 135-136                            79  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            Br     CH 0                                    80  CH(CH.sub.3).sub.2                                                                           H       CH.sub.3                                                                             Cl     CH 0                                    81  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            H      CH 0                                    82  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            NHCH.sub.3                                                                            CH 0                                    83  CH(CH.sub.3 ).sub.2                                                                          H       OCH.sub.3                                                                            NHCH.sub.3                                                                            N  0                                    84  CH(CH.sub.3).sub.2                                                                           H       CH.sub.3                                                                             NHCH.sub.3                                                                            CH 0                                    85  CH(CH.sub.3).sub.2                                                                           H       CH.sub.3                                                                             NHCH.sub.3                                                                            N  0                                    86  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            SCH.sub.3                                                                             CH 0                                    87  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                      CH 0                                    88  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            OC.sub.3 H.sub.7                                                                      CH 0                                    89  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                      N  0                                    90  CH(CH.sub.3).sub.2                                                                           H       Cl    OC.sub.2 H.sub.5                                                                      CH 0                                    91  CH(CH.sub.3).sub.2                                                                           H       OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                      CH 0                                    92  CH(CH.sub.3).sub.2                                                                           H       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                             CH 0                                    93  CH(CH.sub.3).sub.2                                                                           H       CF.sub.3                                                                             OCH.sub.3                                                                             CH 0                                    94  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.2 CF.sub.3                                                                   CH.sub.3                                                                              CH 0                                    95  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             CH 0                                    96  CH(CH.sub.3).sub. 2                                                                          H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.2 CF.sub.3                                                                    CH 0                                    97  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             N  0                                    98  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             N  0                                    99  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.2 CF.sub.3                                                                   NHCH.sub.3                                                                            N  0                                   100  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            NHC.sub.2 H.sub.5                                                                     CH 0                                   101  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.2 CF.sub.3                                                                   NHC.sub.2 H.sub.5                                                                     CH 0                                   102  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                     CH 0                                   103  CH(CH.sub.3).sub.2                                                                           H       OCH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                   CH 0                                   104  CH.sub.2 CH.sub.3                                                                     6-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 162-163                           105  CH.sub.2 CH.sub.3                                                                     6-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 151-152                           106  CH.sub.2 CH.sub.3                                                                     6-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1 128-129                           107  CH.sub.2 CH.sub.3                                                                     6-Cl   H       OCH.sub.3                                                                            Cl     CH 1                                   108  CH.sub.2 CH.sub.3                                                                     6-F    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   109  CH.sub.2 CH.sub.3                                                                     6-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   110  CH.sub.2 CH.sub.3                                                                     6-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   112  CH.sub.2 CH.sub.3                                                                     6-F    H       OCH.sub.3                                                                            Cl     CH 1                                   113  CH.sub.2 CH.sub.3                                                                     6-Br   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   114  CH.sub.2 CH.sub.3                                                                     5-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   115  CH.sub.2 CH.sub.3                                                                     5-Br   H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   116  CH.sub.2 CH.sub.3                                                                     5-Cl   H       OCH.sub.3                                                                            Cl     CH 1                                   117  CH.sub.2 CH.sub.3                                                                     5-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   118  CH.sub.2 CH.sub.3                                                                     4-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   119  CH.sub.2 CH.sub.3                                                                     4-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   120  CH.sub.2 CH.sub.3                                                                     4-Br   H       OCH.sub.3                                                                            Cl     CH 1                                   121  CH.sub.2 CH.sub.3                                                                     3-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 148-149                           122  CH.sub.2 CH.sub.3                                                                     3-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   123  CH.sub.2 CH.sub.3                                                                     6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   124  CH.sub.2 CH.sub.3                                                                     6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   125  CH.sub.2 CH.sub.3                                                                     6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   126  CH.sub.2 CH.sub.3                                                                     6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   127  CH.sub.2 CH.sub.3                                                                     5-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   128  CH.sub.2 CH.sub.3                                                                     5-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   129  CH.sub.2 CH.sub.3                                                                     4-OCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   130  CH.sub.2 CH.sub.3                                                                     4-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   131  CH.sub.2 CH.sub.3                                                                     3-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   132  CH.sub.2 CH.sub.3                                                                     3-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   133  CH.sub.2 CH.sub.3                                                                     6-OC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 194-195                           134  CH.sub.2 CH.sub.3                                                                     6-OC.sub.3 H.sub.7                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   135  CH.sub.2 CH.sub.3                                                                     6-OC.sub.4 H.sub.9                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   136  CH.sub.2 CH.sub.3                                                                     6-SCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   137  CH.sub.2 CH.sub.3                                                                     6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 163                               138  CH.sub.2 CH.sub.3                                                                     6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 148                               139  CH.sub.2 CH.sub.3                                                                     6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub. 3                                                                             N  1                                   140  CH.sub.2 CH.sub.3                                                                     6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1 154-156                           141  CH.sub.2 CH.sub.3                                                                     6-COOC.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 124-125                           142  CH.sub.2 CH.sub.3                                                                     6-COOC.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 128-129                           143  CH.sub.2 CH.sub.3                                                                     5-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   144  CH.sub.2 CH.sub.3                                                                     5-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1                                   145  CH.sub.2 CH.sub.3                                                                     4-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   146  CH.sub.2 CH.sub.3                                                                     4-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   147  CH.sub.2 CH.sub.3                                                                     3-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   148  CH.sub.2 CH.sub.3                                                                     3-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1                                   149  CH.sub.2 CH.sub.3                                                                     6-COOC.sub.3 H.sub.7                                                                  H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   150  CH.sub.2 CH.sub.3                                                                     6-COOC.sub.4 H.sub.9                                                                  H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   151  CH.sub.2 CH.sub.3                                                                     6-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1 139-140                           152  CH.sub.2 CH.sub.3                                                                     6-CH.sub.3                                                                            H       OCH.sub.3                                                                            Cl     CH 1                                   153  CH.sub.2 CH.sub.3                                                                     6-CH.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 177-178                           154  CH.sub.2 CH.sub.3                                                                     6-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 155-156 (decomp.)                 155  CH.sub.2 CH.sub.3                                                                     5-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   156  CH.sub.2 CH.sub.3                                                                     5-CH.sub.3                                                                            H       OCH.sub.3                                                                            Cl     CH 1  82 (decomp.)                     157  CH.sub.2 CH.sub.3                                                                     4-CH.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   158  CH.sub.2 CH.sub.3                                                                     3-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 118-120                           159  CH.sub.2 CH.sub.3                                                                     6-C.sub.2 H.sub.5                                                                     H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1 139-141                           160  CH.sub.2 CH.sub.3                                                                     6-C.sub.3 H.sub.7                                                                     H       OCH.sub.3                                                                            Cl     CH 1 122-124                           161  CH.sub.2 CH.sub.3                                                                     6-C.sub.4 H.sub.9                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   162  CH.sub.2 CH.sub.3                                                                     6-NO.sub.2                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   163  CH.sub.2 CH.sub.3                                                                     6-CF.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1 155-156                           164  CH.sub.2 CH.sub.3                                                                     6-CN   H       OCH.sub.3                                                                            Cl     CH 1                                   165  CH.sub.2 CH.sub.3                                                                     6-SCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   166  CH.sub.2 CH.sub.3                                                                     6-SC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   167  CH.sub.2 CH.sub.3                                                                     6-SC.sub.5 H.sub.9                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   168  CH.sub.2 CH.sub.3                                                                     6-SCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   169  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   170  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   171  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   172  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-Cl   H       OCH.sub.3                                                                            Cl     CH 1                                   173  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-F    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   174  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-F    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   175  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   176  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-F    H       OCH.sub.3                                                                            Cl     CH 1                                   177  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-Br   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   178  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   179  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-Br   H       OCH.sub. 3                                                                           CH.sub.3                                                                              N  1                                   180  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-Cl   H       OCH.sub.3                                                                            Cl     CH 1                                   181  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   182  CH.sub.2 CH.sub.2 CH.sub.3                                                            4-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   183  CH.sub.2 CH.sub.2 CH.sub.3                                                            4-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   184  CH.sub.2 CH.sub.2 CH.sub.3                                                            4-Br   H       OCH.sub.3                                                                            Cl     CH 1                                   185  CH.sub.2 CH.sub.2 CH.sub.3                                                            3-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   186  CH.sub.2 CH.sub.2 CH.sub.3                                                            3-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   187  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   188  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   189  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   190  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   191  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   192  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   193  CH.sub.2 CH.sub.2 CH.sub.3                                                            4-OCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   194  CH.sub.2 CH.sub.2 CH.sub.3                                                            4-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   195  CH.sub.2 CH.sub.2 CH.sub.3                                                            3-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   196  CH.sub.2 CH.sub.2 CH.sub.3                                                            3-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   197  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-OC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   198  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-OC.sub.3 H.sub.7                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   199  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-OC.sub.4 H.sub.9                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   200  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-SCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   201  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   202  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   203  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                    203a                                                                               CH.sub.2 CH.sub.2 CH.sub.3                                                            6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1                                   204  CH.sub. 2 CH.sub.2 CH.sub.3                                                           6-COOC.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   205  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-COOC.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   206  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   207  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1                                   208  CH.sub.2 CH.sub.2 CH.sub.3                                                            4-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   209  CH.sub.2 CH.sub.2 CH.sub.3                                                            4-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   210  CH.sub.2 CH.sub.2 CH.sub.3                                                            3-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   211  CH.sub.2 CH.sub.2 CH.sub.3                                                            3-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1                                   212  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-COOC.sub.3 H.sub.7                                                                  H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   213  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-COOC.sub.4 H.sub.9                                                                  H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   214  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   215  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-CH.sub.3                                                                            H       OCH.sub.3                                                                            Cl     CH 1                                   216  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-CH.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   217  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   218  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   219  CH.sub.2 CH.sub.2 CH.sub.3                                                            5-CH.sub.3                                                                            H       OCH.sub.3                                                                            Cl     CH 1                                   220  CH.sub.2 CH.sub.2 CH.sub.3                                                            4-CH.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   221  CH.sub.2 CH.sub.2 CH.sub.3                                                            3-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   222  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-C.sub.2 H.sub.5                                                                     H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   223  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-C.sub.3 H.sub.7                                                                     H       OCH.sub.3                                                                            Cl     CH 1                                   224  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-C.sub.4 H.sub.9                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   225  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-NO.sub.2                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   226  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-CF.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   227  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-CN   H       OCH.sub.3                                                                            Cl     CH 1                                   228  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-SCH.sub.3                                                                           H       OCH.sub. 3                                                                           OCH.sub.3                                                                             CH 1                                   229  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-SC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   230  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-SC.sub.5 H.sub.9                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   231  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-SCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   232  CH(CH.sub.3).sub.2                                                                    6-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   233  CH(CH.sub.3).sub.2                                                                    6-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   234  CH(CH.sub.3).sub.2                                                                    6-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   235  CH(CH.sub.3).sub.2                                                                    6-Cl   H       OCH.sub.3                                                                            Cl     CH 1                                   236  CH(CH.sub.3).sub.2                                                                    6-F    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   237  CH(CH.sub.3).sub.2                                                                    6-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   238  CH(CH.sub.3).sub.2                                                                    6-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   239  CH(CH.sub.3).sub.2                                                                    6-F    H       OCH.sub.3                                                                            Cl     CH 1                                   240  CH(CH.sub.3).sub.2                                                                    6-Br   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   241  CH(CH.sub.3).sub.2                                                                    5-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   242  CH(CH.sub.3).sub.2                                                                    5-Br   H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   243  CH(CH.sub.3 ).sub.2                                                                   5-Cl   H       OCH.sub.3                                                                            Cl     CH 1                                   244  CH(CH.sub.3).sub.2                                                                    5-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   245  CH(CH.sub.3).sub.2                                                                    4-Cl   H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   246  CH(CH.sub.3).sub.2                                                                    4-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   247  CH(CH.sub.3).sub.2                                                                    4-Br   H       OCH.sub.3                                                                            Cl     CH 1                                   248  CH(CH.sub.3).sub.2                                                                    3-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   249  CH(CH.sub.3).sub.2                                                                    3-F    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   250  CH(CH.sub.3).sub.2                                                                    6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   251  CH(CH.sub.3).sub.2                                                                    6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   252  CH(CH.sub.3).sub.2                                                                    6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   253  CH(CH.sub.3).sub.2                                                                    6-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   254  CH(CH.sub.3).sub.2                                                                    5-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   255  CH(CH.sub.3).sub.2                                                                    5-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   256  CH(CH.sub.3).sub.2                                                                    4-OCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   257  CH(CH.sub.3).sub.2                                                                    4-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   258  CH(CH.sub.3).sub. 2                                                                   3-OCH.sub.3                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   259  CH(CH.sub.3).sub.2                                                                    3-OCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   260  CH(CH.sub.3).sub.2                                                                    6-OC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   261  CH(CH.sub.3).sub.2                                                                    6-OC.sub.3 H.sub.7                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   262  CH(CH.sub.3).sub.2                                                                    6-OC.sub.4 H.sub.9                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   263  CH(CH.sub.3).sub.2                                                                    6-SCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   264  CH(CH.sub.3).sub.2                                                                    6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   265  CH(CH.sub.3).sub.2                                                                    6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   266  CH(CH.sub.3).sub.2                                                                    6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   267  CH(CH.sub.3).sub.2                                                                    6-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1                                   268  CH(CH.sub.3).sub.2                                                                    6-COOC.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   269  CH(CH.sub.3).sub.2                                                                    6-COOC.sub.2 H.sub.5                                                                  H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   270  CH(CH.sub.3).sub.2                                                                    5-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   271  CH(CH.sub.3).sub.2                                                                    5-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1                                   272  CH(CH.sub. 3).sub.2                                                                   4-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   273  CH(CH.sub.3).sub.2                                                                    4-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   274  CH(CH.sub.3).sub.2                                                                    3-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   275  CH(CH.sub.3).sub.2                                                                    3-COOCH.sub.3                                                                         H       OCH.sub.3                                                                            Cl     CH 1                                   276  CH(CH.sub.3).sub.2                                                                    6-COOC.sub.3 H.sub.7                                                                  H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   277  CH(CH.sub.3).sub.2                                                                    6-COOC.sub.4 H.sub.9                                                                  H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   278  CH(CH.sub.3).sub.2                                                                    6-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   279  CH(CH.sub.3).sub.2                                                                    6-CH.sub.3                                                                            H       OCH.sub.3                                                                            Cl     CH 1                                   280  CH(CH.sub.3).sub.2                                                                    6-CH.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   281  CH(CH.sub.3).sub.2                                                                    6-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   282  CH(CH.sub.3).sub.2                                                                    5-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   283  CH(CH.sub.3).sub.2                                                                    5-CH.sub.3                                                                            H       OCH.sub.3                                                                            Cl     CH 1                                   284  CH(CH.sub.3).sub.2                                                                    4-CH.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   285  CH(CH.sub.3).sub.2                                                                    3-CH.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   286  CH(CH.sub.3).sub.2                                                                    6-C.sub.2 H.sub.5                                                                     H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   287  CH(CH.sub.3).sub.2                                                                    6-C.sub.3 H.sub.7                                                                     H       OCH.sub.3                                                                            Cl     CH 1                                   288  CH(CH.sub.3).sub.2                                                                    6-C.sub.4 H.sub.9                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   289  CH(CH.sub.3).sub.2                                                                    6-NO.sub.2                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   290  CH(CH.sub.3).sub.2                                                                    6-CF.sub.3                                                                            H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   291  CH(CH.sub.3).sub.2                                                                    6-CN   H       OCH.sub.3                                                                            Cl     CH 1                                   292  CH(CH.sub.3).sub.2                                                                    6-SCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   293  CH(CH.sub.3).sub.2                                                                    6-SC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            2 3    CH 1                                   294  CH(CH.sub.3).sub.2                                                                    6-SC.sub.5 H.sub.9                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   295  CH(CH.sub.3).sub.2                                                                    6-SCH.sub.3                                                                           H       OCH.sub.3                                                                            Cl     CH 1                                   296  CH.sub.2 CH.sub.3                                                                     4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            Cl     CH 2                                   297  CH.sub.2 CH.sub.3                                                                     4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   298  CH.sub.2 CH.sub.3                                                                     4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            CH.sub.3                                                                              N  2                                   299  CH.sub.2 CH.sub.3                                                                     3,5-Cl.sub.2                                                                          H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   300  CH.sub.2 CH.sub. 2 CH.sub.3                                                           4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            Cl     CH 2                                   301  CH.sub.2 CH.sub.2 CH.sub.3                                                            4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   302  CH.sub.2 CH.sub.2 CH.sub.3                                                            4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 2                                   303  CH.sub.2 CH.sub.2 CH.sub.3                                                            3,5-Cl.sub.2                                                                          H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   304  CH(CH.sub.3).sub.2                                                                    4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            CH.sub.3                                                                              N  2                                   305  CH(CH.sub.3).sub.2                                                                    4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   306  CH(CH.sub.3).sub.2                                                                    4,6-Cl.sub.2                                                                          H       OCH.sub.3                                                                            Cl     CH 2                                   307  CH(CH.sub.3).sub.2                                                                    3,5-Cl.sub.2                                                                          H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   308  CH.sub.2 CH.sub.3                                                                     4,6-F.sub.2                                                                           H       OCF.sub.2 H                                                                          CH.sub.3                                                                              CH 2                                   309  CH.sub.2 CH.sub.3                                                                     4,6-F.sub.2                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   310  CH.sub.2 CH.sub.3                                                                     4,6-F.sub.2                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  2                                   311  CH.sub.2 CH.sub.3                                                                     3,5-F.sub.2                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   312  CH.sub.2 CH.sub.2 CH.sub.2                                                            4,6-F.sub.2                                                                           H       OCH.sub.3                                                                            Cl     CH 2                                   313  CH.sub.2 CH.sub.2 CH.sub.3                                                            4,6-F.sub.2                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   314  CH.sub.2 CH.sub.2 CH.sub.3                                                            4,6-F.sub.2                                                                           H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 2                                   315  CH.sub.2 CH.sub.2 CH.sub.3                                                            3,5-F.sub.2                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   316  CH(CH.sub.3).sub.2                                                                    4,6-F.sub.2                                                                           H       OCH.sub.3                                                                            CH.sub.3                                                                              N  2                                   317  CH(CH.sub.3).sub.2                                                                    4,6-F.sub.2                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   318  CH.sub.2 CH.sub.3                                                                     4,6-(CH.sub.3).sub.2                                                                  H       OCH.sub.3                                                                            Cl     CH 2                                   319  CH.sub.2 CH.sub.3                                                                     4,6-(CH.sub.3).sub.2                                                                  H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 2                                   320  CH.sub.2 CH.sub.3                                                                     3,5-(NO.sub.2).sub.2                                                                  H       OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             CH 2                                   321  CH.sub.2 CH.sub.3                                                                     H      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0 119-120                           322  CH.sub.2 CH.sub.3                                                                     H      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  0 101-102                           323  CH.sub.2 CH.sub.3                                                                     H      CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0                                   324  CH.sub.2 CH.sub.3                                                                     H      CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                                                            Cl     CH 0                                   325  CH.sub.2 CH.sub.2 CH.sub.3                                                            H      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0                                   326  CH.sub.2 CH.sub.2 CH.sub. 3                                                           H      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              CH 0                                   327  CH.sub.2 CH.sub.2 CH.sub.3                                                            H      CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0                                   328  CH.sub.2 CH.sub.2 CH.sub.3                                                            H      CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                                                            CH.sub.3                                                                              N  0                                   329  CH(CH.sub.3).sub.2                                                                    H      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0 127-130                           330  CH(CH.sub.3).sub.2                                                                    H      CH.sub.3                                                                               OCH.sub.3                                                                            Cl     CH 0                                   331  CH(CH.sub.3).sub.2                                                                    H      CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0                                   332  CH(CH.sub.3).sub.2                                                                    H      CH.sub.2 CHCH.sub.2                                                                    OCF.sub.2 H                                                                          CH.sub.3                                                                              CH 0                                   333  CH.sub.2 CH.sub.3                                                                     H      C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0                                   334  CH.sub.2 CH.sub.2 CH.sub.3                                                            H      C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            Cl     CH 0                                   335  CH(CH.sub.3).sub.2                                                                    H      C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0                                   336  CH.sub.2 CH.sub.3                                                                     H      C.sub.2 H.sub.5                                                                        OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             CH 0                                   337  CH.sub.2 CH.sub.2 CH.sub.3                                                            H      C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                             CH 0                                   338  CH.sub.2 CH.sub.3                                                                     6-CH.sub.3                                                                            CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   339  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-OCH.sub.3                                                                           CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   340  CH(CH.sub.3).sub.2                                                                    6-Cl   CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                                                            Cl     CH 1                                   341  CH.sub.2 CH.sub.3                                                                     6-F    CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   342  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-CF.sub.3                                                                            CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                             N  1                                   343  CH(CH.sub.3).sub.2                                                                    6-COOCH.sub.3                                                                         CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   344  CH.sub.2 CH.sub.3                                                                     6-C.sub.2 H.sub.5                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 166-167                           345  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 155-156                           346  "      "      H       OCH.sub.3                                                                            Cl     CH 1                                   347  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1                                   348  "      "      H       OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                    N  1                                   349  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   350  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   351  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1                                   352  "      "      H       OCH.sub.3                                                                            OCH.sub.3                                                                             N  1                                   353  "      6-C.sub.3 H.sub.7                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 158                               354  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 148                               355  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1 124-126                           356  "      "      H       OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                                                            N  1 167-169                           357  "      "      H       OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                    N  1 115-117                           358  "      "      H       CH.sub.3                                                                             Cl     CH 1  90 (decomp.)                     359  "      6-OC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 157-158                           360  "      "      H       OCH.sub.3                                                                            Cl     CH 1 158-159                           361  CH.sub.2 CH.sub.3                                                                     6-OC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1 166-167                           362  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1 139-140                           363  "      "      H       OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                    N  1 124                               364  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 112-115                           365  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   366  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1                                   367  "      "      H       OCH.sub.3                                                                            OCH.sub.3                                                                             N  1 150-151 (decomp.)                 368  "      6-CF.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 181                               369  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 151-153                           370  "      "      H       OCH.sub.3                                                                            Cl     CH 1                                   371  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1                                   372  "      "      H       OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                    N  1                                   373  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   374  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   375  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1                                   376  "      "      H       OCH.sub.3                                                                            OCH.sub.3                                                                             N  1                                   377  "      6-CH.sub.3                                                                            CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1  88 (decomp.)                     378  "      5-CH.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 158-161                           379  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 113 (decomp.)                     380  "      5-C.sub.2 H.sub.5                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   381  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   382  "      5-Cl   H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   383  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   384  "      5-OCH.sub.3                                                                           H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   385  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   386  "      6-CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 102-105 (decomp.)                 387  "      "      H       OCH.sub.3                                                                            OCH.sub.3                                                                             N  1 154-155                           388  CH.sub.2 CH.sub.2 CH.sub.3                                                            6-C.sub.2 H.sub.5                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   389  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   390  "      "      H       OCH.sub.3                                                                            Cl     CH 1                                   391  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1                                   392  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   393  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   394  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1                                   395  "      6-C.sub. 3 H.sub.7                                                                    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 143-145                           396  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   397  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   398  "      6-OC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 138-139                           399  "      "      H       OCH.sub.3                                                                            Cl     CH 1                                   400  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   401  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1                                   402  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 111-113                           403  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   404  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1                                   405  "      6-CF.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 165-166                           406  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   407  "      "      H       OCH.sub.3                                                                            Cl     CH 1                                   408  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1                                   409  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   410  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1 121-122                           411  "      6-CH.sub.3                                                                            CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   412  "      6-CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   413  CH(CH.sub.3).sub.2                                                                    6-C.sub.2 H.sub.5                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   414  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   415  "      "      H       OCH.sub.3                                                                            Cl     CH 1                                   416  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1                                   417  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   418  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   419  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1                                   420  "      6-C.sub.3 H.sub.7                                                                     H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 137                               421  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1 131-133                           422  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   423  "      6-OC.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 129-130                           424  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   425  "      "      H       OCH.sub.3                                                                            Cl     CH 1                                   426  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   427  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1                                   428  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   429  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                              N  1                                   430  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1                                   431  "      6-CF.sub.3                                                                            H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1 157-159                           432  "      "      H       OCH.sub.3                                                                            CH.sub.3                                                                              CH 1                                   433  "      "      H       OCH.sub.3                                                                            Cl     CH 1                                   434  "      "      H       CH.sub.3                                                                             CH.sub.3                                                                              CH 1                                   435  "      "      CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   436  "      "      H       OCF.sub.2 H                                                                          OCF.sub.2 H                                                                           CH 1                                   437  "      6-CH.sub.3                                                                            CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   438  "      6-CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   439  CH.sub.2 CH.sub.3                                                                     3,4,6-F.sub.3                                                                         H       OCH.sub.3                                                                            OCH.sub.3                                                                             CH 3                                   440  "      6-Cl   C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   441  "      6-OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                             CH 1                                   442  "      "      C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                             N  1                                   443  CH.sub.2 CH.sub.2 CH.sub.2                                                            "      C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                             N  1                                   __________________________________________________________________________

                  TABLE 2                                                          ______________________________________                                          ##STR14##                                                                     Ex. No.                                                                               R.sup.1     R.sup.2  R.sup.5                                                                               n   m.p. [°C.]                       ______________________________________                                         444    CH.sub.2 CH.sub.3                                                                          H        CH.sub.3                                                                              0                                           445    CH.sub.2 CH.sub.3                                                                          H        H      0                                           446    CH.sub.2 CH.sub.3                                                                          H        OCH.sub.3                                                                             0                                           447    CH.sub.2 CH.sub.2 CH.sub.3                                                                 H        CH.sub.3                                                                              0                                           448    CH.sub.2 CH.sub.2 CH.sub.3                                                                 H        H      0                                           449    CH.sub.2 CH.sub.2 CH.sub.3                                                                 H        OCH.sub.3                                                                             0                                           450    CH(CH.sub.3).sub.2                                                                         H        CH.sub.3                                                                              0                                           451    CH(CH.sub.3).sub.2                                                                         H        H      0                                           452    CH(CH.sub.3).sub.2                                                                         H        OCH.sub.3                                                                             0                                           453    CH.sub.2 CH.sub.3                                                                          6-CH.sub.3                                                                              OCH.sub.3                                                                             1                                           454    CH.sub.2 CH.sub.2 CH.sub.3                                                                 6-OCH.sub.3                                                                             OCH.sub.3                                                                             1                                           455    CH(CH.sub.3).sub.2                                                                         6-Cl     OCH.sub.3                                                                             1                                           456    CH.sub.2 CH.sub.3                                                                          6-CF.sub.3                                                                              OCH.sub.3                                                                             1                                           457    CH.sub.2 CH.sub.2 CH.sub.3                                                                 6-F      OCH.sub.3                                                                             1                                           458    CH(CH.sub.3).sub.2                                                                         6-OCF.sub.2 H                                                                           OCH.sub.3                                                                             1                                           ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR15##                                                                     Ex. No.                                                                               R.sup.1    R.sup.2  R.sup.5                                                                              G    n   m.p. [°C.]                    ______________________________________                                         459    CH.sub.2 CH.sub.3                                                                         H        CH.sub.3                                                                             CH.sub.2                                                                            0                                        460    CH.sub.2 CH.sub.3                                                                         H        H     CH.sub.2                                                                            0                                        461    CH.sub.2 CH.sub.3                                                                         H        OCH.sub.3                                                                            CH.sub.2                                                                            0                                        462    CH.sub.2 CH.sub.2 CH.sub.3                                                                H        CH.sub.3                                                                             CH.sub.2                                                                            0                                        463    CH.sub.2 CH.sub.2 CH.sub.3                                                                H        H     CH.sub.2                                                                            0                                        464    CH.sub.2 CH.sub.2 CH.sub.3                                                                H        OCH.sub.3                                                                            CH.sub.2                                                                            0                                        465    CH(CH.sub.3).sub.2                                                                        H        CH.sub.3                                                                             CH.sub.2                                                                            0                                        466    CH(CH.sub.3).sub.2                                                                        H        H     CH.sub.2                                                                            0                                        467    CH(CH.sub.3).sub.2                                                                        H        OCH.sub.3                                                                            CH.sub.2                                                                            0                                        468    CH.sub.2 CH.sub.3                                                                         H        CH.sub.3                                                                             O    0                                        469    CH.sub.2 CH.sub.3                                                                         H        H     O    0                                        470    CH.sub.2 CH.sub.3                                                                         H        OCH.sub.3                                                                            O    0                                        471    CH.sub.2 CH.sub.2 CH.sub.3                                                                H        CH.sub.3                                                                             O    0                                        472    CH.sub.2 CH.sub.2 CH.sub.3                                                                H        H     O    0                                        473    CH.sub.2 CH.sub.2 CH.sub.3                                                                H        OCH.sub.3                                                                            O    0                                        474    CH(CH.sub.3).sub.2                                                                        H        CH.sub.3                                                                             O    0                                        475    CH(CH.sub.3).sub.2                                                                        H        H     O    0                                        476    CH(CH.sub.3).sub.2                                                                        H        OCH.sub.3                                                                            O    0                                        477    CH.sub.2 CH.sub.3                                                                         6-CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.2                                                                            1                                        478    CH.sub.2 CH.sub.2 CH.sub.3                                                                6-OCH.sub.3                                                                             CH.sub.3                                                                             O    1                                        479    CH(CH.sub.3).sub.2                                                                        6-Cl     CH.sub.3                                                                             CH.sub.2                                                                            1                                        480    CH.sub.2 CH.sub.3                                                                         6-CF.sub.3                                                                              CH.sub.3                                                                             O    1                                        481    CH.sub.2 CH.sub.2 CH.sub.3                                                                6-F      CH.sub.3                                                                             CH.sub.2                                                                            1                                        482    CH(CH.sub.3).sub.2                                                                        6-OCF.sub.2 H                                                                           CH.sub.3                                                                             O    1                                        ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR16##                                                                     Ex. No. R.sup.1     R.sup.2   R.sup.5                                                                               n    m.p.                                 ______________________________________                                         483     CH.sub.2 CH.sub.3                                                                          H         CH.sub.3                                                                              0                                         484     CH.sub.2 CH.sub.3                                                                          H         H      0                                         485     CH.sub.2 CH.sub.3                                                                          H         OCH.sub.3                                                                             0                                         486     CH.sub.2 CH.sub.2 CH.sub.3                                                                 H         CH.sub.3                                                                              0                                         487     CH.sub.2 CH.sub.2 CH.sub.3                                                                 H         H      0                                         488     CH.sub.2 CH.sub.2 CH.sub.3                                                                 H         OCH.sub.3                                                                             0                                         489     CH(CH.sub.3).sub.2                                                                         H         CH.sub.3                                                                              0                                         490     CH(CH.sub.3).sub.2                                                                         H         H      0                                         491     CH(CH.sub.3).sub.2                                                                         H         OCH.sub.3                                                                             0                                         492     CH.sub.2 CH.sub.3                                                                          6-CH.sub.3                                                                               OCH.sub.3                                                                             1                                         493     CH.sub.2 CH.sub.2 CH.sub.3                                                                 6-OCH.sub.3                                                                              OCH.sub.3                                                                             1                                         494     CH(CH.sub.3).sub.2                                                                         6-Cl      OCH.sub.3                                                                             1                                         495     CH.sub.2 CH.sub.3                                                                          6-CF.sub.3                                                                               OCH.sub.3                                                                             1                                         496     CH.sub.2 CH.sub.2 CH.sub.3                                                                 6-F       OCH.sub.3                                                                             1                                         497     CH(CH.sub.3).sub.2                                                                         6-OCF.sub.2 H                                                                            OCH.sub.3                                                                             1                                         ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR17##                                                                     Ex. No. R.sup.1    R.sup.2   R.sup.5                                                                              R7   n   m.p.                               ______________________________________                                         498     CH.sub.2 CH.sub.3                                                                         H         CH.sub.3                                                                             CH.sub.3                                                                            0                                      499     CH.sub.2 CH.sub.3                                                                         H         H     CH.sub.3                                                                            0                                      500     CH.sub.2 CH.sub.3                                                                         H         OCH.sub.3                                                                            CH.sub.3                                                                            0                                      501     CH.sub.2 CH.sub.3                                                                         H         CH.sub.3                                                                             H    0                                      502     CH.sub.2 CH.sub.2 CH.sub.3                                                                H         CH.sub.3                                                                             CH.sub.3                                                                            0                                      503     CH.sub.2 CH.sub.2 CH.sub.3                                                                H         H     CH.sub.3                                                                            0                                      504     CH.sub.2 CH.sub.2 CH.sub.3                                                                H         OCH.sub.3                                                                            CH.sub.3                                                                            0                                      505     CH.sub.2 CH.sub.2 CH.sub.3                                                                H         CH.sub.3                                                                             H    0                                      506     CH(CH.sub.3).sub.2                                                                        H         CH.sub.3                                                                             CH.sub.3                                                                            0                                      507     CH(CH.sub.3 ).sub.2                                                                       H         H     CH.sub.3                                                                            0                                      508     CH(CH.sub.3).sub.2                                                                        H         OCH.sub.3                                                                            CH.sub.3                                                                            0                                      509     CH(CH.sub.3).sub.2                                                                        H         CH.sub.3                                                                             H    0                                      510     CH.sub.2 CH.sub.3                                                                         6-CH.sub.3                                                                               CH.sub.3                                                                             H    1                                      511     CH.sub.2 CH.sub.2 CH.sub.3                                                                6-OCH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3                                                                            1                                      512     CH(CH.sub.3).sub.2                                                                        6-Cl      CH.sub.3                                                                             H    1                                      513     CH.sub.2 CH.sub.3                                                                         6-CF.sub.3                                                                               CH.sub.3                                                                             CH.sub.3                                                                            1                                      514     CH.sub.2 CH.sub.2 CH.sub.3                                                                6-F       CH.sub.3                                                                             H    1                                      515     CH(CH.sub.3).sub.2                                                                        6-OCF.sub.2 H                                                                            CH.sub.3                                                                             CH.sub.3                                                                            1                                      ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR18##                                                                     Ex.                                                                            No.  R.sup.1    R.sup.2  R.sup.5                                                                              R.sup.6                                                                              E    n   m.p.                             ______________________________________                                         516  CH.sub.2 CH.sub.3                                                                         H        OCH.sub.3                                                                            OCH.sub.3                                                                            CH   0                                    517  CH.sub.2 CH.sub.3                                                                         H        OCH.sub.3                                                                            CH.sub.3                                                                             CH   0                                    518  CH.sub.2 CH.sub.3                                                                         H        OCH.sub.3                                                                            CH.sub.3                                                                             N    0                                    519  CH.sub.2 CH.sub.2 CH.sub.3                                                                H        OCH.sub.3                                                                            OCH.sub.3                                                                            CH   0                                    520  CH.sub.2 CH.sub.2 CH.sub.3                                                                H        OCH.sub.3                                                                            CH.sub.3                                                                             CH   0                                    521  CH.sub.2 CH.sub.2 CH.sub.3                                                                H        OCH.sub.3                                                                            CH.sub.3                                                                             N    0                                    522  CH(CH.sub.3).sub.2                                                                        H        OCH.sub.3                                                                            OCH.sub.3                                                                            CH   0                                    523  CH(CH.sub.3).sub. 2                                                                       H        OCH.sub.3                                                                            CH.sub.3                                                                             CH   0                                    524  CH(CH.sub.3).sub.2                                                                        H        OCH.sub.3                                                                            CH.sub.3                                                                             N    1                                    525  CH.sub.2 CH.sub.3                                                                         6-CH.sub.3                                                                              OCH.sub.3                                                                            CH.sub.3                                                                             N    1                                    526  CH.sub.2 CH.sub.2 CH3                                                                     6-OCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH   1                                    527  CH(CH.sub.3).sub.2                                                                        6-Cl     OCH.sub.3                                                                            OCH.sub.3                                                                            N    1                                    528  CH.sub.2 CH.sub.3                                                                         6-CF.sub.3                                                                              OCH.sub.3                                                                            CH.sub.3                                                                             CH   1                                    529  CH.sub.2 CH.sub.2 CH.sub.3                                                                6-F      OCH.sub.3                                                                            OCH.sub.3                                                                            N    1                                    530  CH(CH.sub.3).sub.2                                                                        6-OCF.sub.2 H                                                                           OCH.sub.3                                                                            CH.sub.3                                                                             CH   1                                    ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                          ##STR19##                                                                     Ex. No. R.sup.1     R.sup.2   R.sup.8                                                                               n    m.p.                                 ______________________________________                                         531     CH.sub.2 CH.sub.3                                                                          H         OCH.sub.3                                                                             0                                         532     CH.sub.2 CH.sub.3                                                                          H         CH.sub.3                                                                              0                                         533     CH.sub.2 CH.sub.2 CH.sub.3                                                                 H         OCH.sub.3                                                                             0                                         534     CH.sub.2 CH.sub.2 CH.sub.3                                                                 H         CH.sub.3                                                                              0                                         535     CH(CH.sub.3).sub.2                                                                         H         OCH.sub.3                                                                             0                                         536     CH(CH.sub.3).sub.2                                                                         H         CH.sub.3                                                                              0                                         537     CH.sub.2 CH.sub.3                                                                          6-CH.sub.3                                                                               CH.sub.3                                                                              1                                         538     CH.sub.2 CH.sub.2 CH.sub.3                                                                 6-OCH.sub.3                                                                              CH.sub.3                                                                              1                                         539     CH(CH.sub.3).sub.2                                                                         6-Cl      OCH.sub.3                                                                             1                                         540     CH.sub.2 CH.sub.3                                                                          6-CF.sub.3                                                                               CH.sub.3                                                                              1                                         541     CH.sub.2 CH.sub.2 CH.sub.3                                                                 6-F       OCH.sub.3                                                                             1                                         542     CH(CH.sub. 3).sub.2                                                                        6-OCF.sub.2 H                                                                            CH.sub.3                                                                              1                                         ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                          ##STR20##                                                                     Ex.                                                                            No.   R.sup.1    R.sup.2  R.sup.7                                                                             R.sup.8                                                                              R.sup.11                                                                            n   m.p.                             ______________________________________                                         543   CH.sub.2 CH.sub.3                                                                         H        H    OCH.sub.3                                                                            H    0                                    544   CH.sub.2 CH.sub.3                                                                         H        H    CH.sub.3                                                                             CH.sub.3                                                                            0                                    545   CH.sub.2 CH.sub.3                                                                         H        CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                            0                                    546   CH.sub.2 CH.sub.2 CH.sub.3                                                                H        H    OCH.sub.3                                                                            H    0                                    547   CH.sub.2 CH.sub.2 CH.sub.3                                                                H        H    CH.sub.3                                                                             CH.sub.3                                                                            0                                    548   CH.sub.2 CH.sub.2 CH.sub.3                                                                H        CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                            0                                    549   CH(CH.sub.3).sub.2                                                                        H        H    OCH.sub.3                                                                            H    0                                    550   CH(CH.sub.3).sub.2                                                                        H        H    CH.sub.3                                                                             CH.sub.3                                                                            0                                    551   CH(CH.sub.3).sub.2                                                                        H        CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                            0                                    552   CH.sub.2 CH.sub.3                                                                         6-CH.sub.3                                                                              H    CH.sub.3                                                                             H    1                                    553   CH.sub.2 CH.sub.2 CH.sub.3                                                                6-OCH.sub.3                                                                             H    CH.sub.3                                                                             CH.sub.3                                                                            1                                    554   CH(CH.sub.3).sub.2                                                                        6-Cl     CH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                            1                                    555   CH.sub.2 CH.sub.3                                                                         6-CF.sub.3                                                                              H    CH.sub.3                                                                             H    1                                    556   CH.sub.2 CH.sub.3                                                                         6-F      H    OCH.sub.3                                                                            CH.sub.3                                                                            1                                    557   CH(CH.sub.3).sub.2                                                                        6-Cl     CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                            1                                    ______________________________________                                    

BIOLOGICAL EXAMPLES

The damage on the weed plants and the tolerance by crop plants were scored using a key where numbers from 0 to 5 express the activity. In this key

0 denotes no action

1 denotes 0-20% action or damage

2 denotes 20-40% action or damage

3 denotes 40-60% action or damage

4 denotes 60-80% action or damage

5 denotes 80-100% action or damage

1. Pre-emergence action on weeds

Seeds or rhizome pieces of monocotyledon and dicotyledon weed plants were placed in plastic pots containing sandy loam soil and covered with soil. Various dosages of aqueous suspensions or emulsions of the compounds according to the invention formulated as wettable powders or emulsion concentrates were then applied to the surface of the cover soil, at an application rate of water of 600-800 l/ha (converted).

After the treatment, the pots were placed in the greenhouse and maintained at good growth conditions for the weeds. Visual scoring of the damage to plants or of the emergence damage was carried out after the emergence of the test plants after a trial period of 3 to 4 weeks, comparing them to untreated control plants. As shown by the score data in Table 9, the compounds according to the invention have good herbicidal pre-emergence activity against a broad range of weed grasses and broad leaf weeds.

2. Post-emergence action on weeds

Seeds or rhizome pieces of monocotyledon and dicotyledon weeds were placed in plastic pots in sandy loam ground, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated in the three-leaf stage.

Various dosages of the compounds according to the invention formulated as wettable powders or emulsion concentrates were sprayed onto the green parts of the plants, at an application rate of water of 600-800 l/ha (converted), and the action of the preparations was scored visually after the test plants had remained in the greenhouse for about 3 to 4 weeks under optimum growth conditions, comparing them to untreated control plants.

The agents according to the invention exhibit a good herbicidal activity against a broad range of economically important weed grasses and broad-leaf weeds, also in the post-emergence treatment (Table 10).

3. Tolerance by crop plants

In further greenhouse experiments, seeds of a relatively large number of crop plants and weeds were placed in sandy loam ground and covered with soil.

Some of the pots were treated immediately as described under 1., those remaining were placed in the greenhouse until the plants had developed two to three true leaves and were then sprayed with various dosages of the substances according to the invention as described under 2.

Four to five weeks after application, with the plants remaining in the greenhouse, visual scoring revealed that the compounds according to the invention did not cause any damage to dicotyledon crops, such as, for example, soya beans, cotton, oilseed rape, sugar beet and potatoes when applied both as a pre-emergence and post-emergence treatment, even at high dosages of active substance. Furthermore, Gramineae crops such as, for example, barley, wheat, rye, sorghum millet, maize or rice, were also unaffected by some of the substances. Thus, the compounds of the formula I exhibit high selectivity on application for controlling undesired plant growth in agricultural crops.

                  TABLE 9                                                          ______________________________________                                         Pre-emergence action of the compounds according                                to the invention                                                               Ex.  Dosage in No.                                                                              Herbicidal action                                             No.  Kg of a.i./ha                                                                              SIA    CRS  STM  AS   ECG   LOM                               ______________________________________                                          2   0,6         5      5    5    1    3     4                                  3   0,6         5      5    5    2    3     3                                  4   0,6         5      5    4    4    4     1                                  5   0,6         5      4    4    2    2     1                                  7   0,6         5      5    3    2    2     2                                  75  0,6         5      5    5    2    2     2                                 104  0,3         5      5    5    1    3     1                                 133  0.3         5      5    5    4    5     5                                 137  0,3         5      5    5    2    4     2                                 138  0,3         5      5    5    5    4     5                                 153  0,3         5      5    5    3    3     4                                 163  0,3         5      5    5    4    4     5                                 321  0,3         5      5    5    1    2     1                                 ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                         Post-emergence action of the compounds                                         according to the invention                                                     Ex.  Dosage in No.                                                                              Herbicidal action                                             No.  Kg of a.i./ha                                                                              SIA    CRS  STM  AS   ECG   LOM                               ______________________________________                                          2   0,6         5      5    5    0    4     5                                  3   0,6         5      5    5    1    4     4                                  4   0,6         5      4    4    3    4     2                                  5   0,6         5      5    4    2    2     3                                  7   0,6         5      5    5    1    3     2                                  75  0,6         5      5    5    0    5     3                                 104  0,3         5      5    5    3    4     3                                 133  0,3         5      5    5    3    5     5                                 137  0,3         5      4    5    2    4     2                                 138  0,3         5      5    5    4    5     4                                 153  0,3         5      4    5    2    4     2                                 163  0,3         5      5    5    4    4     5                                 321  0,3         4      5    5    1    3     1                                 ______________________________________                                          Abbreviations:                                                                 SIA = Sinapis alba-                                                            CRS = Chrysanthemum segetum-                                                   STM = Stellaria media-                                                         AS = Avena sativa-                                                             ECG = Echinochloa crus-galli-                                                   LOM = Lolium multiflorum-                                                     a.i. = active substance                                                   

We claim:
 1. A compound of formula I, or a salt thereof, ##STR21## wherein R¹ is ethyl, propyl or isopropyl,R² is halogen, NO₂, CF₃, CN, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, (C₁ -C₄)alkylthio or [(C₁ -C₄)alkoxy]carbonyl, n is 0, 1, 2 or 3, Y is O or S, R³ is hydrogen, (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl, (C₂ -C₈)alkynyl, or (C₁ -C₄)alkoxy, R⁴ is heterocyclic radical of the formula ##STR22## E is CH R⁵ and R⁶ independently of one another are hydrogen, (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy, (C₁ -C₆)alkylthio, it being possible for the above-mentioned alkyl-containing radicals to be monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by (C₁ -C₄)alkoxy, or (C₁ -C₄)alkylthio, or furthermore are a radical of formula NR¹² R¹³, --OCHR⁷ --CO₂ R¹², (C₃ -C₆)cycloalkyl, (C₃ -C₅)alkenyl, (C₂ -C₄)alkynyl, (C₃ -C₅)alkenyloxy or (C₃ -C₅)alkynyloxy, R⁷ is hydrogen or (C₁ -C₄)alkyl, and R¹² and R¹³ independently of one another are hydrogen, (C₁ -C₄)alkyl, (C₂ -C₄)alkenyl or (C₃ -C₄)alkynyl.
 2. A compound of the formula I or a salt thereof as claimed in claim 1, whereinn is 0 or 1, Y is O, R² is oriented in the 6-position of the phenyl ring and is fluorine, chlorine, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy or [(C₁ -C₄)alkoxy]-carbonyl, R³ is hydrogen, (C₁ -C₄)alkyl, (C₃ -C₄)alkenyl, R⁴ is a heterocyclic radical of the formula ##STR23## and R⁵ and R⁶ independently of one another are (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, (C₁ -C₄)alkylthio, it being possible for the above-mentioned alkyl-containing radicals to be monosubstituted or polysubstituted in the alkyl moiety by halogen or monosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio.
 3. A compound as claimed in claim 2, wherein R⁵ and R⁶ independently of one another are methyl or methoxy.
 4. A compound as claimed in claim 2 wherein R¹ is CH₂ CH₃, R² is 6-COOCH₃, R³ is H, R⁵ is OCH₃, R⁶ is CH₃, E is CH and n is
 1. 5. A compound as recited in claim 2, wherein R¹ is CH₂ CH₃, R² is CF₃, R³ is H, R⁵ is OCH₃, R⁶ is CH₃, E is CH and n is
 1. 6. A compound as recited in claim 1, wherein R¹ is CH₂ CH₃, R² is CF₃, R³ is H, R⁴ is ##STR24## R⁵ is OCH₃, R⁶ is CH₃, E is CH and n is
 1. 7. A herbicidal composition comprising a herbicidally effective amount of one or more compounds as claimed in claim 1, or salts thereof, and an inert carrier therefor.
 8. A plant growth regulating composition comprising a plant growth regulating effective amount of one or more compounds as claimed in claim 1, or salts thereof, and an inert carrier therefor.
 9. A method for controlling noxious plants which comprises applying a herbicidally effective amount of one or more compounds as claimed in claim 1, or salts thereof, to a noxious plant or soil used in agriculture or industry.
 10. A method for regulating the growth of crop plants which comprises applying a growth regulating effective amount of one or more compounds as claimed in claim 1, or salts thereof, to a crop plant or an area of cultivation of said crop plant.
 11. A compound as in claim 2, wherein Y is oxygen, and R³ is hydrogen, and n is 0 or 1, and R⁵ and R⁶ independently of one another are (C₁ -C₄)alkyl or (C₁ -C₄)alkoxy.
 12. A compound as in claim 11, wherein R¹ is ethyl, n is 0, R⁵ is methoxy and R⁶ is methoxy.
 13. A compound as in claim 11, wherein R¹ is isopropyl, n is 0, R⁵ is methoxy and R⁶ is methoxy.
 14. A compound as in claim 11, wherein R¹ is ethyl, n is 1, R² is 6-chloro, R⁵ is methoxy and R⁶ is methoxy.
 15. A compound as in claim 11, wherein R¹ is ethyl, n is 1, R² is 6-chloro, R⁵ is methoxy and R⁶ is methoxy.
 16. A compound as in claim 11, wherein R¹ is ethyl, n is 1, R² is 6-methoxy, R⁵ is methoxy and R⁶ is methoxy.
 17. A compound as in claim 11, wherein R¹ is ethyl, n is 1, R² is 6-methyl, R⁵ is methoxy and R⁶ is methoxy.
 18. A compound as in claim 11, wherein R¹ is ethyl, n is 1, R² is 6-methoxycarbonyl, R⁵ is methoxy and R⁶ is methoxy. 